DE1193037B - Process for the preparation of N- (polyhaloalkanesulfenyl) -sulphonic acid amides - Google Patents
Process for the preparation of N- (polyhaloalkanesulfenyl) -sulphonic acid amidesInfo
- Publication number
- DE1193037B DE1193037B DEF39754A DEF0039754A DE1193037B DE 1193037 B DE1193037 B DE 1193037B DE F39754 A DEF39754 A DE F39754A DE F0039754 A DEF0039754 A DE F0039754A DE 1193037 B DE1193037 B DE 1193037B
- Authority
- DE
- Germany
- Prior art keywords
- acid amides
- acid
- preparation
- sulfonic acid
- polyhaloalkanesulfenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 amine salts Chemical class 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229940124530 sulfonamide Drugs 0.000 claims description 5
- 150000003456 sulfonamides Chemical class 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 230000000855 fungicidal effect Effects 0.000 description 3
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 3
- SVDVKEBISAOWJT-UHFFFAOYSA-N n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1 SVDVKEBISAOWJT-UHFFFAOYSA-N 0.000 description 3
- RYFZYYUIAZYQLC-UHFFFAOYSA-N perchloromethyl mercaptan Chemical compound ClSC(Cl)(Cl)Cl RYFZYYUIAZYQLC-UHFFFAOYSA-N 0.000 description 3
- 150000003449 sulfenic acid halides Chemical class 0.000 description 3
- 206010061217 Infestation Diseases 0.000 description 2
- 241000227653 Lycopersicon Species 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241001454295 Tetranychidae Species 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- RUFAFKWLURMVKG-UHFFFAOYSA-N 1,2,2,2-tetrachloroethyl thiohypochlorite Chemical compound ClSC(Cl)C(Cl)(Cl)Cl RUFAFKWLURMVKG-UHFFFAOYSA-N 0.000 description 1
- HPWUIVNEYXRBJW-UHFFFAOYSA-N 1,2,2-trichloroethyl thiohypochlorite Chemical compound ClC(C(Cl)Cl)SCl HPWUIVNEYXRBJW-UHFFFAOYSA-N 0.000 description 1
- SGDAONFFHUCRON-UHFFFAOYSA-N 1-chloro-n-phenylmethanesulfonamide Chemical compound ClCS(=O)(=O)NC1=CC=CC=C1 SGDAONFFHUCRON-UHFFFAOYSA-N 0.000 description 1
- IXQQODJESGRDGF-UHFFFAOYSA-N 2,3-dichloro-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(Cl)=C1Cl IXQQODJESGRDGF-UHFFFAOYSA-N 0.000 description 1
- SURQJARFZVYLFJ-UHFFFAOYSA-N 4-chloro-n-propan-2-ylbenzenesulfonamide Chemical compound CC(C)NS(=O)(=O)C1=CC=C(Cl)C=C1 SURQJARFZVYLFJ-UHFFFAOYSA-N 0.000 description 1
- BJKNXDSKYOQVTJ-UHFFFAOYSA-N 4-nitro-n-phenylbenzenesulfonamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=CC=C1 BJKNXDSKYOQVTJ-UHFFFAOYSA-N 0.000 description 1
- 241000213004 Alternaria solani Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- QECVIPBZOPUTRD-UHFFFAOYSA-N N=S(=O)=O Chemical class N=S(=O)=O QECVIPBZOPUTRD-UHFFFAOYSA-N 0.000 description 1
- 241000233679 Peronosporaceae Species 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- 241001281803 Plasmopara viticola Species 0.000 description 1
- 241001123569 Puccinia recondita Species 0.000 description 1
- 241001246061 Puccinia triticina Species 0.000 description 1
- 241001464837 Viridiplantae Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- UHNHTTIUNATJKL-UHFFFAOYSA-N n-methylmethanesulfonamide Chemical compound CNS(C)(=O)=O UHNHTTIUNATJKL-UHFFFAOYSA-N 0.000 description 1
- MFIKMLPQWQBFLD-UHFFFAOYSA-N n-phenylmethanesulfonamide;sodium Chemical compound [Na].CS(=O)(=O)NC1=CC=CC=C1 MFIKMLPQWQBFLD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/08—Sulfenic acids; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
Deutsche Kl.: 12 ο-23/03 German class: 12 ο -23/03
Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:Number:
File number:
Registration date:
Display day:
1193 037
F39754IVb/12o
10. November 1959
20. Mai 19651193 037
F39754IVb / 12o
November 10, 1959
May 20, 1965
Die Erfindung betrifft ein Verfahren zur Herstellung von N-(Polyhalogenalkansulfenyl)-sulfonsäureamiden, welches dadurch gekennzeichnet ist, daß man Sulfonsäureamide der allgemeinen FormelThe invention relates to a process for the preparation of N- (polyhaloalkanesulfenyl) sulfonic acid amides, which is characterized in that one sulfonic acid amides of the general formula
R' — SO2-NH-R"R '- SO 2 -NH-R "
in der R' und R" einen aliphatischen, cycloaliphatischen, araliphatischen oder aromatischen Rest bedeuten und R' auch eine Dialkylaminogruppe sein kann, entweder in Form ihrer Alkali- oder Aminsalze ίο in Abwesenheit basischer Mittel oder in Form der freien Sulfonamide in Gegenwart von 1 Mol eines säurebindenden Mittels in inerten Lösungsmitteln mit Polyhalogenalkansulfensäurehalogeniden, die im Alkylrest mindestens 2 Kohlenstoffatome und an den zum Schwefelatom α- und ^-ständigen Kohlenstoffatomen insgesamt mindestens 2 Halogenatome enthalten, umsetzt.in which R 'and R "denote an aliphatic, cycloaliphatic, araliphatic or aromatic radical and R 'can also be a dialkylamino group, either in the form of its alkali or amine salts ίο in the absence of basic agents or in the form of the free sulfonamides in the presence of 1 mole of one acid-binding agent in inert solvents with Polyhalogenalkansulfensäurehalogeniden im Alkyl radical at least 2 carbon atoms and on the carbon atoms α and ^ to the sulfur atom contain a total of at least 2 halogen atoms.
Aus den deutschen Patentschriften 887 506 und 921 290 ist schon bekannt, daß Trichlormethansulfensäurechlorid (Perchlormethylmercaptan) mit Sulfonsäureamiden in Gegenwart säurebindender Mittel entsprechende N-Trichlormethylsulfenylderivate bildet. Die dort genannten Verbindungen sind zur Bekämpfung von Pilzkrankheiten insbesondere auf Blättern grüner Pflanzen geeignet. Auch die aus trisubstituierten Sulfurylamiden und Perchlormethylmercaptan erhältlichen Verbindungen (vgl. die deutsche Patentschrift 975 295) weisen gute blattfungizide Eigenschaften auf.It is already known from German patents 887 506 and 921 290 that trichloromethanesulfenic acid chloride (Perchloromethyl mercaptan) with sulfonic acid amides in the presence of acid-binding agents Medium corresponding N-trichloromethylsulfenyl derivatives forms. The compounds mentioned there are particularly useful for combating fungal diseases suitable on leaves of green plants. Also those made from trisubstituted sulfurylamides and perchloromethyl mercaptan Compounds obtainable (cf. German Patent 975 295) have good leaf fungicides Properties on.
Die erfindungsgemäß erhältlichen N-(Polyhalogenalkansulfenyl)-sulfonsäureamide zeichnen sich durch beachtliche biocide, besonders fungicide Eigenschaften aus.The N- (polyhaloalkanesulfenyl) sulfonic acid amides obtainable according to the invention are characterized by considerable biocidal, especially fungicidal properties.
Sie weisen ein breiteres biologisches Wirkungsspektrum als die bekannten N-Trichlormethylsulfenylderivate und insbesondere bei Rostkrankheiten eine erhöhte Wirksamkeit auf (vgl. Spalte 5, Verbindungen 4 und 10).They have a broader biological spectrum of activity than the known N-trichloromethylsulfenyl derivatives and especially in the case of rust diseases, an increased effectiveness (cf. column 5, compounds 4 and 10).
Verfahren zur Herstellung von N-(Polyhalogenalkansulfenyl)-sulfonsäureamiden Process for the preparation of N- (polyhaloalkanesulfenyl) -sulphonic acid amides
Anmelder:Applicant:
Farbenfabriken Bayer Aktiengesellschaft,Paint factories Bayer Aktiengesellschaft,
LeverkusenLeverkusen
Als Erfinder benannt:
Dr. Klaus Sasse, Köln-Stammheim;
Dr. Richard Wegler, Leverkusen;
Dr. Paul-Ernst Frohberger,
Dr. Ferdinand Grewe,
Burscheid (Bez. Düsseldorf)Named as inventor:
Dr. Klaus Sasse, Cologne-Stammheim;
Dr. Richard Wegler, Leverkusen;
Dr. Paul-Ernst Frohberger,
Dr. Ferdinand Grewe,
Burscheid (District Düsseldorf)
Neben den guten blattfungjciden Eigenschaften zeigen die neuen Verbindungen insbesondere ausgezeichnete Wirksamkeit gegen Rostkrankheiten an Getreide, zum Teil auch gegen Insekten und Spinnmilben, während entsprechende N-Trichlormethylsulfenyl-Verbindungen an diesen Schädlingen praktisch völlig wirkungslos sind.In addition to the good foliar fungicidal properties, the new compounds are particularly excellent Effectiveness against rust diseases on grain, partly also against insects and spider mites, while corresponding N-trichloromethylsulfenyl compounds are practically completely ineffective on these pests.
Die erfindungsgemäße Umsetzung der Sulfensäurehalogenide mit Sulfonsäureamiden, die am Stickstoffatom der Sulfonamidgruppe noch wenigstens ein Wasserstoffatom enthalten, z. B. dem Methansulfonsäuremethylamid, dem Chlormethansulfonsäureanilid, dem Benzolsulfonsäuremethylamid, dem 4-Chlorbenzolsulfonsäure-isopropylamid, dem 4-Nitrobenzolsulfonsäureanilid oder dem Dimethylamin-N-sulfonsäureanilid verläuft im Sinne der folgenden Gleichung, wobei Verbindungen gemäß der allgemeinen Formel I entstehen.The inventive reaction of the sulfenic acid halides with sulfonic acid amides, which are on the nitrogen atom the sulfonamide group still contain at least one hydrogen atom, e.g. B. methanesulfonic acid methylamide, the chloromethanesulfonic acid anilide, the benzenesulfonic acid methylamide, the 4-chlorobenzenesulfonic acid isopropylamide, the 4-nitrobenzenesulfonic acid anilide or the dimethylamine-N-sulfonic acid anilide proceeds in the sense of the following Equation whereby compounds according to general formula I are formed.
R' —SO2-NH + Hai —S —R R"R '—SO 2 -NH + Hai —S —R R "
•. R' — SO2 — N — S — R ■+ Halogenwasserstoff
R"•. R '- SO 2 - N - S - R ■ + hydrogen halide
R "
In dieser Formel steht R für einen Alkylrest mit mindestens 2 Kohlenstoffatomen, der an den zum Schwefelatom α- und ^-ständigen Kohlenstoffatomen wenigstens 2 Halogenatome gebunden enthält, R' und R" stehen für einen aliphatischen, cycloaliphatischen, araliphatischen oder aromatischen Rest, und R' steht auch für eine Dialkylaminogruppe. .In this formula, R stands for an alkyl radical having at least 2 carbon atoms, which is attached to the Sulfur atom α and ^ carbon atoms contains at least 2 halogen atoms bonded, R ' and R "stands for an aliphatic, cycloaliphatic, araliphatic or aromatic radical, and R 'also represents a dialkylamino group. .
Als Polyhalogenalkansulfensäurehalogenide können z. B. das 1,2,2,2'Tetrachloräthan-, das 2,2,2-Trichloräthan- und das 1,2,2-Trichloräthansulfensäurechlorid verwendet werden.As Polyhalogenalkansulfensäurehalogenide z. B. the 1,2,2,2'Tetrachloräthan-, the 2,2,2-Trichloräthan- and 1,2,2-trichloroethanesulfenic acid chloride be used.
Die Herstellung der Verbindungen der allgemeinen Formel I erfolgt in inerten Lösungsmitteln, indem entweder Alkali- oder Aminsalze der SulfonamideThe compounds of general formula I are prepared in inert solvents by either alkali or amine salts of the sulfonamides
509 570/428509 570/428
mit den Sulfensäurehalogeniden in Abwesenheit Amine, mit den Sulfensäurehalogeniden reagierenreact with the sulfenic acid halides in the absence of amines, with the sulfenic acid halides
basischer Mittel umgesetzt werden oder aber in der läßt.basic agents are implemented or in the leaves.
Weise, daß man die freien Sulfonamide in Gegenwart Die guten fungiciden Eigenschaften der N-(PoIy-Way that the free sulfonamides in the presence of the good fungicidal properties of the N- (poly-
säurebindender Mittel, wie Alkali- oder Erdalkali- halogenalkansulfenyl)-sulfonamide gehen aus folgen-Acid-binding agents, such as alkali or alkaline earth haloalkanesulfenyl) sulfonamides are based on the following
hydroxyde oder -carbonate, Alkoholate oder tertiäre 5 den biologischen Prüfungsbefunden hervor:Hydroxyde or carbonates, alcoholates or tertiary 5 highlight the biological test results:
1. Infektionsversuch mit Phytophthora infestans an Tomaten (Befallsgrad in % gegenüber unbehandelter Kontrolle = 100)1st infection test with Phytophthora infestans on tomatoes (degree of infection in% compared to untreated control = 100)
Wirkstoffkonzentration 0,05% O,O25o/oActive ingredient concentration 0.05% O, O25o / o
WirkstoffstrukturDrug structure
CH3-SO2-NCH 3 -SO 2 -N
^S-CHCl-CCl3 ^ S-CHCl-CCl 3
— CHCl — CHCfe- CHCl - CHCfe
Γ^υνΊ pnΓ ^ υνΊ pn
2. Infektionsversuch mit Peronospora (Plasmopara viticola) an Reben2. Attempted infection with downy mildew (Plasmopara viticola) on vines
WirkstoffstrukturDrug structure
0,05%0.05%
WirkstoflkonzentrationActive ingredient concentration
0,025% 0,0125%0.025% 0.0125%
(CHs)2N-SO2-N Kontrolle(CHs) 2 N-SO 2 -N control
100100
100100
100100
3. Infektionsversuch mit Alternaria solani an Tomaten3. Attempted infection with Alternaria solani on tomatoes
WirkstoffstrukturDrug structure
0,0125%0.0125%
WirkstoffkonzentrationActive ingredient concentration
0,003% 0,0015%0.003% 0.0015%
(CHs)2N-SO2-N Kontrolle(CHs) 2 N-SO 2 -N control
CHCl-CHCI2CHCl-CHCl2
100100
100100
100100
4. Infektionsversuch mit Braunrost an Weizen (Puccinia triticina) und Roggen (Puccinia dispersa) (0 = keine Wirkung; + = mäßige Wirkung, schwacher Befall; ++ = volle Wirkung, ohne Befall)4th infection experiment with brown rust on wheat (Puccinia triticina) and rye (Puccinia dispersa) (0 = no effect; + = moderate effect, weak infestation; ++ = full effect, no infestation)
WirkstoffstrukturDrug structure
Weizenbraunrost
WirkstoffkonzentrationWheat brown rust
Active ingredient concentration
0,3% 0,1% 0,03% 0,003%0.3% 0.1% 0.03% 0.003%
Roggenbraunrost Wirkstoffkonzentration 0,3% 0,1% 0,03%Brown rust rye active ingredient concentration 0.3% 0.1% 0.03%
CH3-SO2-NCH 3 -SO 2 -N
Cl S-CHCl-CHCl2 Cl S-CHCl-CHCl 2
ClCH2-SO2-NClCH 2 -SO 2 -N
SO2-NSO 2 -N
Ns-CHCI-CCI3 Ns-CHCI-CCI 3
/CH3 / CH 3
Ns — CHCl-CCl3 Ns - CHCl-CCl 3
SO2-N SO2-NSO 2 -N SO 2 -N
/CH3
S-CHCl-CHCl2 / CH 3
S-CHCl-CHCl 2
^s-CHCI-CHCI2 ^ s-CHCI-CHCI 2
^-CHCl-CCl3 ^ -CHCl-CCl 3
SO2-NSO 2 -N
/CH3 / CH 3
Ns-.Ns-.
/CH3
^S-CHCl-CCl3 / CH 3
^ S-CHCl-CCl 3
(CHs)2N-SO2-N; ^—' (CHs) 2 N-SO 2 -N; ^ - '
XS —CHCl-CCI3 X S -CHCl-CCI 3
(CHa)2N-SO2-N(CHa) 2 N-SO 2 -N
Vergleich:Comparison:
^s-CHCI-CHCI2 ^ s-CHCI-CHCI 2
r/CHs ^S-CCl3 r / CHs ^ S-CCl 3
0,3%Wirl
0.3%
Ktoffkonzentratü
0,1%Wheat b
Fuel concentrate
0.1%
jn in der Spritzb
0,03%rust
jn in the spray booth
0.03%
0,003%Quiet
0.003%
CH3/ I ^=/
S-CCl3 ^ N- SO 2 - N- / S
CH 3 / I ^ = /
S-CCl 3
5. Spinnmilben werden durch 2%ige Spritzmittel von N-Methyl- N - (1,2,2,2 -tetrachloräthyl)-sulfenyl- und N - Methyl - N - (1,2,2 - trichloräthyl) - sulfenyl-(3,4-dichlorbenzol)-sulfamid innerhalb 24 Stunden 100%ig abgetötet.5. Spider mites are sprayed with 2% N-methyl- N - (1,2,2,2 -tetrachloroethyl) -sulfenyl- and N - methyl - N - (1,2,2 - trichloroethyl) sulfenyl (3,4-dichlorobenzene) sulphamide 100% killed within 24 hours.
In eine Suspension von 19,3 g Methansulfonsäureanilid-natrium in 200 ml Benzol tropft man bei Raumtemperatur unter Rühren 23,5 g 1,2,2,2-Tetrachloräthansulfensäurechlorid ein. Dann wird noch ^Stunde bei 30 bis 400C nachgerührt, das Unlösliche abgesaugt und das Filtrat unter vermindertem Druck eingedampft. Als Rückstand verbleiben 26 g (entsprechend 78% der Theorie) N-(1,2,2,2-Tetrachloräthansulfenyl)-methansulfonsäureanilid der Formel 23.5 g of 1,2,2,2-tetrachloroethanesulfenic acid chloride are added dropwise at room temperature with stirring to a suspension of 19.3 g of sodium methanesulfonic acid anilide in 200 ml of benzene. The mixture is then stirred for a further ^ hour at 30 to 40 ° C., the insolubles are filtered off with suction and the filtrate is evaporated under reduced pressure. The residue left is 26 g (corresponding to 78% of theory) of N- (1,2,2,2-tetrachloroethanesulfenyl) methanesulphonic acid anilide of the formula
CH3-SO2-NCH 3 -SO 2 -N
S-CHCl-CCl3 S-CHCl-CCl 3
IOIO
2020th
die nach dem Umkristallisieren aus Ligroin bei F. = 94 bis 960C schmilzt.which, after recrystallization from ligroin, melts at a temperature of 94 to 96 ° C.
In analoger Weise werden erhalten:In an analogous way the following are obtained:
N-(2,2,2-Trichloräthansulfenyl)-methansulfon-N- (2,2,2-trichloroethanesulfenyl) -methanesulphone-
säureanilid, F. = 138 0C (Benzol).
N-( 1 ^,^-Tetrachloräthansulfenyty-chlor-acid anilide, m.p. = 138 0 C (benzene).
N- (1 ^, ^ - Tetrachlorethansulfenyty-chlor-
methansulfonsäurenilid (hellgelbes öl).methanesulfonic acid silide (light yellow oil).
N-( 1 ^^-Trichloräthansulfenyty-methansulfon-N- (1 ^^ - Trichloräthansulfenyty-methanesulfon-
säure-p-chloranilid, F. 84 bis 860C (Ligroin). N-( 1 ^^-Tetrachloräthansulfenyty-benzyl-acid-p-chloroanilide, m.p. 84 to 86 0 C (ligroin). N- (1 ^^ - tetrachloroethanesulfenyty-benzyl-
sulfonsäuremethylamid (hellgelbes öl).
N-( 1 ^^-TrichloräthansulfenyO-benzolsulfon-sulfonic acid methylamide (light yellow oil).
N- (1 ^^ - TrichloräthansulfenyO-benzenesulfone-
säuremethylamid (hellgelbes öl).
N-(2,2,2-Trichloräthansulfenyl)-benzolsulfon-acid methylamide (light yellow oil).
N- (2,2,2-trichloroethanesulfenyl) -benzenesulphone-
säuremethylamid, F. = 45 bis 47° C.
N-( 1 ^,^-Tetrachloräthansulfenyiybenzol-acid methylamide, m.p. 45 to 47 ° C.
N- (1 ^, ^ - Tetrachlorethansulfenyiybenzol-
sulfonsäureisopropylamid,F. = 110bislll°C (Ligroin).sulfonic acid isopropylamide, F. = 110 to III ° C (Ligroin).
N-O^^-TetrachloräthansulfenylH^dichlorbenzolsulfonsäuremethylamid, F. = 88 bisN-O ^^ - TetrachlorethansulfenylH ^ dichlorobenzenesulphonic acid methylamide, F. = 88 to
9O0C (Ligroin).
N-( 1 ^^^-Tetrachloräthansulfenyl^nitro-9O 0 C (ligroin).
N- (1 ^^^ - tetrachloroethanesulfenyl ^ nitro-
benzolsulfonsäuremethylamid, F. = 110 bisbenzenesulfonic acid methylamide, m.p. = 110 bis
112°C (Benzol/Ligroin).
' N'-( 1 ^^-Trichloräthansulfenyty-dimethylamin-N-sulfonsäureanilid,
F. = 56 bis 570C112 ° C (benzene / ligroin).
'N' - (1 ^^ - Trichloräthansulfenyty-dimethylamine-N-sulfonic acid anilide, F. = 56 to 57 0 C
(Ligroin).
N'-(2,2,2-Trichloräthansulfenyl)-dimethylamin-N-sulfonsäureanilid,
F. = 59 bis 6I0C(Ligroin).
N '- (2,2,2-Trichloräthansulfenyl) -dimethyl-amine-N-sulfonsäureanilid, F. = 59 0 C to 6I
(Ligroin).
N-( 1 ^^^-Tetrachloräthansulfenyl-S-nitro-(Ligroin).
N- (1 ^^^ - tetrachloroethanesulfenyl-S-nitro-
benzolsulfonsäuremethylamid, F. = 100 bis 1020C (Benzol/Ligroin).benzenesulfonic acid methylamide, m.p. = 100 to 102 0 C (benzene / ligroin).
Claims (1)
Schweizerische Patentschrift Nr. 342 564;
USA.-Patentschrift Nr. 2 779 788.Considered publications:
Swiss Patent No. 342 564;
U.S. Patent No. 2,779,788.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF39754A DE1193037B (en) | 1959-11-10 | 1959-11-10 | Process for the preparation of N- (polyhaloalkanesulfenyl) -sulphonic acid amides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF39754A DE1193037B (en) | 1959-11-10 | 1959-11-10 | Process for the preparation of N- (polyhaloalkanesulfenyl) -sulphonic acid amides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1193037B true DE1193037B (en) | 1965-05-20 |
Family
ID=7097923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF39754A Pending DE1193037B (en) | 1959-11-10 | 1959-11-10 | Process for the preparation of N- (polyhaloalkanesulfenyl) -sulphonic acid amides |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1193037B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3869509A (en) * | 1969-10-23 | 1975-03-04 | Bayer Ag | N-alkyl-N(trihalomethylthio)-sulfamic acid chloride |
| FR2333783A1 (en) * | 1975-11-25 | 1977-07-01 | Cheminova As | ORGANIC FLUOROIMIDES, THEIR PREPARATION AND THEIR USE AS FUNGICIDES AND ACARICIDES |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2779788A (en) * | 1952-10-31 | 1957-01-29 | Geigy Ag J R | Trichloromethane sulphenic acid derivatives |
| CH342564A (en) * | 1955-04-07 | 1959-11-30 | Bayer Ag | Process for the preparation of derivatives of perchloromethyl mercaptan |
-
1959
- 1959-11-10 DE DEF39754A patent/DE1193037B/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2779788A (en) * | 1952-10-31 | 1957-01-29 | Geigy Ag J R | Trichloromethane sulphenic acid derivatives |
| CH342564A (en) * | 1955-04-07 | 1959-11-30 | Bayer Ag | Process for the preparation of derivatives of perchloromethyl mercaptan |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3869509A (en) * | 1969-10-23 | 1975-03-04 | Bayer Ag | N-alkyl-N(trihalomethylthio)-sulfamic acid chloride |
| FR2333783A1 (en) * | 1975-11-25 | 1977-07-01 | Cheminova As | ORGANIC FLUOROIMIDES, THEIR PREPARATION AND THEIR USE AS FUNGICIDES AND ACARICIDES |
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